IE84607B1 - Derivatives of N-Phenylpyrazoles - Google Patents
Derivatives of N-Phenylpyrazoles Download PDFInfo
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- IE84607B1 IE84607B1 IE2002/0481A IE20020481A IE84607B1 IE 84607 B1 IE84607 B1 IE 84607B1 IE 2002/0481 A IE2002/0481 A IE 2002/0481A IE 20020481 A IE20020481 A IE 20020481A IE 84607 B1 IE84607 B1 IE 84607B1
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- WITMXBRCQWOZPX-UHFFFAOYSA-N 1-phenylpyrazole Chemical class C1=CC=NN1C1=CC=CC=C1 WITMXBRCQWOZPX-UHFFFAOYSA-N 0.000 title claims abstract description 6
- 239000000203 mixture Substances 0.000 claims abstract description 62
- -1 cyclic imide Chemical class 0.000 claims abstract description 24
- 230000001069 nematicidal Effects 0.000 claims abstract description 4
- 230000000507 anthelmentic Effects 0.000 claims abstract description 3
- 230000000842 anti-protozoal Effects 0.000 claims abstract 2
- 150000001875 compounds Chemical class 0.000 claims description 69
- 241000238421 Arthropoda Species 0.000 claims description 34
- 241000607479 Yersinia pestis Species 0.000 claims description 18
- 241000244206 Nematoda Species 0.000 claims description 16
- 239000003085 diluting agent Substances 0.000 claims description 8
- 239000000969 carrier Substances 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- 239000003814 drug Substances 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 206010037075 Protozoal infection Diseases 0.000 claims 1
- 239000003904 antiprotozoal agent Substances 0.000 claims 1
- 201000001181 parasitic helminthiasis infectious disease Diseases 0.000 claims 1
- 238000002560 therapeutic procedure Methods 0.000 claims 1
- 125000005034 trifluormethylthio group Chemical group FC(S*)(F)F 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 abstract description 10
- 150000002367 halogens Chemical group 0.000 abstract description 9
- 125000000217 alkyl group Chemical group 0.000 abstract description 8
- 125000004093 cyano group Chemical group *C#N 0.000 abstract description 7
- 238000002360 preparation method Methods 0.000 abstract description 7
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract description 4
- 125000004435 hydrogen atoms Chemical group [H]* 0.000 abstract description 3
- 125000004453 alkoxycarbonyl group Chemical group 0.000 abstract description 2
- 125000001589 carboacyl group Chemical group 0.000 abstract description 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract description 2
- 239000001257 hydrogen Substances 0.000 abstract description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract description 2
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 abstract 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 abstract 1
- 125000004946 alkenylalkyl group Chemical group 0.000 abstract 1
- 125000005038 alkynylalkyl group Chemical group 0.000 abstract 1
- 125000005017 substituted alkenyl group Chemical group 0.000 abstract 1
- 125000004426 substituted alkynyl group Chemical group 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 20
- 239000000243 solution Substances 0.000 description 19
- 241000196324 Embryophyta Species 0.000 description 17
- 241001465754 Metazoa Species 0.000 description 17
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 15
- 239000007787 solid Substances 0.000 description 15
- YMWUJEATGCHHMB-UHFFFAOYSA-N methylene dichloride Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 10
- 241000254173 Coleoptera Species 0.000 description 9
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
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- 239000000126 substance Substances 0.000 description 7
- 239000000725 suspension Substances 0.000 description 7
- QFMDFTQOJHFVNR-UHFFFAOYSA-N 1-[2,2-dichloro-1-(4-ethylphenyl)ethyl]-4-ethylbenzene Chemical compound C1=CC(CC)=CC=C1C(C(Cl)Cl)C1=CC=C(CC)C=C1 QFMDFTQOJHFVNR-UHFFFAOYSA-N 0.000 description 6
- 241000238876 Acari Species 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N acetic acid ethyl ester Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 239000004615 ingredient Substances 0.000 description 6
- CSNNHWWHGAXBCP-UHFFFAOYSA-L mgso4 Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
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- IAYPIBMASNFSPL-UHFFFAOYSA-N oxane Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- YXFVVABEGXRONW-UHFFFAOYSA-N toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 5
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- IAZDPXIOMUYVGZ-UHFFFAOYSA-N dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
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- 230000037406 food intake Effects 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 239000008079 hexane Substances 0.000 description 3
- 239000000391 magnesium silicate Substances 0.000 description 3
- 229910052919 magnesium silicate Inorganic materials 0.000 description 3
- 235000019792 magnesium silicate Nutrition 0.000 description 3
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 3
- 235000019341 magnesium sulphate Nutrition 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000004563 wettable powder Substances 0.000 description 3
- 239000000080 wetting agent Substances 0.000 description 3
- MDLAHYBEAWGVRV-UHFFFAOYSA-N 5-(trifluoromethylsulfanyl)-1H-pyrazole Chemical compound FC(F)(F)SC=1C=CNN=1 MDLAHYBEAWGVRV-UHFFFAOYSA-N 0.000 description 2
- 241000251468 Actinopterygii Species 0.000 description 2
- 229910002012 Aerosil® Inorganic materials 0.000 description 2
- 239000005995 Aluminium silicate Substances 0.000 description 2
- PZZYQPZGQPZBDN-UHFFFAOYSA-N Aluminium silicate Chemical compound O=[Al]O[Si](=O)O[Al]=O PZZYQPZGQPZBDN-UHFFFAOYSA-N 0.000 description 2
- 241000254175 Anthonomus grandis Species 0.000 description 2
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- 206010060969 Arthropod infestation Diseases 0.000 description 2
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- 208000003495 Coccidiosis Diseases 0.000 description 2
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- 241000223924 Eimeria Species 0.000 description 2
- 210000001035 Gastrointestinal Tract Anatomy 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 241000238631 Hexapoda Species 0.000 description 2
- 241000577496 Hypothenemus hampei Species 0.000 description 2
- HJOVHMDZYOCNQW-UHFFFAOYSA-N Isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 2
- 206010023076 Isosporiasis Diseases 0.000 description 2
- 240000008415 Lactuca sativa Species 0.000 description 2
- 241000258916 Leptinotarsa decemlineata Species 0.000 description 2
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- NHQDETIJWKXCTC-UHFFFAOYSA-N Meta-Chloroperoxybenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 2
- 235000002637 Nicotiana tabacum Nutrition 0.000 description 2
- 240000008962 Nicotiana tabacum Species 0.000 description 2
- SNQQPOLDUKLAAF-UHFFFAOYSA-N Nonylphenol Chemical group CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 2
- 241000238887 Ornithodoros Species 0.000 description 2
- 241000283898 Ovis Species 0.000 description 2
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- 210000003491 Skin Anatomy 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M Sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 240000003829 Sorghum propinquum Species 0.000 description 2
- 235000011684 Sorghum saccharatum Nutrition 0.000 description 2
- 240000008529 Triticum aestivum Species 0.000 description 2
- 235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 description 2
- 238000007792 addition Methods 0.000 description 2
- 125000004644 alkyl sulfinyl group Chemical group 0.000 description 2
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- 125000004414 alkyl thio group Chemical group 0.000 description 2
- 235000012211 aluminium silicate Nutrition 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 239000000921 anthelmintic agent Substances 0.000 description 2
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- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
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- LYCAIKOWRPUZTN-UHFFFAOYSA-N glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
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- KWOLFJPFCHCOCG-UHFFFAOYSA-N methylphenylketone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
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- NLYAJNPCOHFWQQ-UHFFFAOYSA-N oxo-oxoalumanyloxy-[oxo(oxoalumanyloxy)silyl]oxysilane;dihydrate Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 2
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- RQYLOOVORNJDQX-UHFFFAOYSA-N trifluoromethyl thiohypochlorite Chemical compound FC(F)(F)SCl RQYLOOVORNJDQX-UHFFFAOYSA-N 0.000 description 2
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- RLLPVAHGXHCWKJ-HKUYNNGSSA-N (3-phenoxyphenyl)methyl (1R,3R)-3-(2,2-dichloroethenyl)-2,2-dimethylcyclopropane-1-carboxylate Chemical compound CC1(C)[C@@H](C=C(Cl)Cl)[C@H]1C(=O)OCC1=CC=CC(OC=2C=CC=CC=2)=C1 RLLPVAHGXHCWKJ-HKUYNNGSSA-N 0.000 description 1
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- DUIOKRXOKLLURE-UHFFFAOYSA-N 2-octylphenol Chemical compound CCCCCCCCC1=CC=CC=C1O DUIOKRXOKLLURE-UHFFFAOYSA-N 0.000 description 1
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- HRZFUMHJMZEROT-UHFFFAOYSA-L 7681-57-4 Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 1
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- 235000013616 tea Nutrition 0.000 description 1
- CJDWRQLODFKPEL-UHFFFAOYSA-N teflubenzuron Chemical compound FC1=CC=CC(F)=C1C(=O)NC(=O)NC1=CC(Cl)=C(F)C(Cl)=C1F CJDWRQLODFKPEL-UHFFFAOYSA-N 0.000 description 1
- 239000012085 test solution Substances 0.000 description 1
- YFNCATAIYKQPOO-UHFFFAOYSA-N thiophanate Chemical compound CCOC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OCC YFNCATAIYKQPOO-UHFFFAOYSA-N 0.000 description 1
- 230000002588 toxic Effects 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 125000004665 trialkylsilyl group Chemical group 0.000 description 1
- 229940078499 tricalcium phosphate Drugs 0.000 description 1
- 229910000391 tricalcium phosphate Inorganic materials 0.000 description 1
- 235000019731 tricalcium phosphate Nutrition 0.000 description 1
- NFACJZMKEDPNKN-UHFFFAOYSA-N trichlorfon Chemical compound COP(=O)(OC)C(O)C(Cl)(Cl)Cl NFACJZMKEDPNKN-UHFFFAOYSA-N 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 235000020234 walnut Nutrition 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
- 239000004562 water dispersible granule Substances 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Abstract
ABSTRACT N-Phenylpyrazole derivatives of the formula: wherein R1 represents cyano, nitro, halogen, acetyl or formyl; Oifig Na bPaitinni The Patents Office R2 represents R5 S02, R5SO or RSS in which R5 is optionally halogen substituted alkyl, alkenyl or alkynyl; R3 represents a hydrogen atom or a group NR6R7 wherein R6 and R7 each represent hydrogen, alkyl, alkenylalkyl, alkynylalkyl, formyl, optionally halogen substituted alkanoyl, optionally halogen substituted alkoxycarbonyl, or alkoxymethyleneamino, halogen, or R6 and R7 together form a cyclic imide and R4 represents a substituted phenyl group possess arthropodicidal, plant nematocidal, anthelmintic and anti-protozoal properties; their preparation, compositions containing them and their use are described.
Description
Derivatives of N—phenylpyrazoles BASF Agro BV Arnhem (NL) wadenswil Branch S This invention relates to an N-phenylpyrazole derivative, to compositions containing it a.nd to its use against arthropod, plant nematode, helminth and protozoan pests. Q EP-A-201 852 (Bayer) discloses, as insecticides, acaricides and nematocides, l—aryl~5-arninopyrazoles, in which the 3-position is unsubstituted or substituted by an alkyl or haloalkyl group and the 4-position is substituted by alkyl, aralkyl or aryl sulphenyl, sulphinyl or sulphonyl.
EP-A-245 875 (also Bayer) discloses, as acaricides, l-arylcyano arninopyrazoles in which the 3-position is substituted by alkyl sulphenyl, sulphinyl or sulphonyl.
The applicant's earlier patent application EP-A-234,119 which was published after the priority date of the present application discloses a method for the control of arthropod, plant nematode or helminth pests using compounds of formula: wherein Y is halogen, cyano, nitro, RSO2, RSO or R8 in which R is alkyl, cycloalkyl or alkenyl, thiocyanato, sulphamoyl, carbamoyl, alkoxycarbonyl, alkanoyl or alkyl; Z represents hydrogen, an amino group -NR'R2, alkylsulphenylarnino, alkoxymethyleneamino, halogen, aIkyl,earboxy1, alkylthio, alkylsulphinyl or alkylsulphonyl, trialkylsilylmethyl, trialkylsilyl, cyano or njtro; R’ represents halogen, alkyl or alkoxy, halogen-substituted alkylthio or alkylsulphinyl, njtro, cyano or alkylsulphonyl; R‘ represents halogen, cyano, nitro, alkyl or cycloallcyl; and n is 1 to 5, and salts thereof, provided that R‘, Y and Z do not simultaneously represent one of nitro, cyano, halogen and unsubstituted alkyl.
The present invention provides an N-phenylpyrazole derivative of formula (I) in which R‘ represents a cyano group; R2 represents a group R5802 in which R‘ represents a trifluorornethyl group; R3 represents an amino group; and R‘ represents a ,6-dichloroe4-trifluoromethylphenyl group, i.e. the compound CF3SO CN / N HZN N CF3 This compound has valuable activity against arthropod, plant nematode, helminth and protozoan pests, more particularly by ingestion of the compound of fonnula (I) by arthropods.
The compound of formula (1), compositions containing it and methods for its use constitute features of the present invention.
According to a feature of the present invention, there is provided a method for the control of arthropod, plant nematode, helminth or protozoan pests at a locus which comprises the treatment of the locus (e.g. by application or administration) with an effective amount of the compound of formula (I).
The compound of formula (I) may, in particular, be used in the field of veterinary medicine and livestock husbandry and in the maintenance of public health against arthropods, helminths or protozoa which are parasitic internally or externally upon .vertebrates, particularly warmfblooded vertebrates, for example man and domestic animals, e.g. cattle, sheep, goats, equines, swine, poultry, dogs, cats and fishes, for example Acarina, including ticks (e.g. Ixodes spp., Boophilus spp. e.g. Boophilus microplus, Amblyomma spp., Hxalomma spp., Rhipicephalus spp. e.g.
Rhipicephalus appgndiculatus, Haemaphysalis spp., Dermacentor spp., Ornithodorus spp. (e.g. Ornithodorus moubata and mites (e.g. Damalinia spp., Dermahyssus gallinae, Sarcoptes spp. e.g. Sarcoptes scabiei, Psoroptes spp., Chorioptes spp., Demodex spp., Eutrombicula spp.,); Diptera (e.g. ggggg spp., Anopheles spp., Mgsga spp., Hypoderma spp., Gasterophilus spp., Simulium spp.); Hemiptera (e.g.
Triatoma spp.); Phthiraptera (e.g. Damalinia spp., Linognathus spp.); Siphonaptera (e.g. Ctenocephalides spp.); Dictyoptera (e.g. Periplaneta spp., Blatella spp.); Hymenoptera (e.g. Monomorium pharaonis); for example against infections of the gastro-intestinal tract caused by parasitic nematode worms, for example members of the family Trichostrongylidae, Nippostronqylus brasiliensis, Trichinella spiralis, Haemonchus contortus, Trichostrongylus colubriformis, Nematodirus battus, Ostertagia circumcincta, Trichostrongylus axgi, Cooperia spp. and Hymenolepis gang; in the control and treatment of protozoal diseases caused by, for example, Eimeria spp. e.g.
Eimeria tenella, Eimeria acervulina, Eimeria brunetti, Eimeria maxima and Eimeria necatrix, Trypanosoma cruzi, Leishmania spp., Plasmodium spp., Babesia spp., Trichomonadidae spp., Histomonas spp., Giardia spp., Toxoplasma spp., Entamoeba histolytica and Theileria spp.; in the protection of stored products, for example cereals, including grain and flour, groundnuts, animal feedstuffs, timber and household goods, e.g. carpets and textiles, against attack by arthropods, more especially beetles, including weevils, moths and mites, for example Ephestia spp. (flour moths), Anthrenus spp. (carpet beetles), Tribolium spp. (flour beetles), Sitophilus spp. (grain weevils) and Acarus spp. _ 15 Plutella gylostella (diamond back moth); against adult and larvae of Coleoptera (beetles) e.g. Hypothenemus hampei (coffee berry borer), Hzlesinus spp. (bark beetles), Anthonomus grandis (cotton boll weevil), Acalygma spp. (cucumber beetles), gggg spp., Psylliodes sppr, Leptinotarsa decemlineata (Colorado potato beetle), Diabrotica spp. (corn rootworms), Gonocephalum spp. (false wire worms), Agriotes spp. (wireworms), Dermolepida and Heteronxchus sppL (white grubs), Phaedon cochleariae (mustard beetle), Lissorhoptrus orzzophilus (rice water weevil), Meligethes spp. (pollen beetles), Ceutorh1nchus.spp., Rhzgchophorus and Cosmopolites spp. (root weevils); against Hemiptera e.g. Psylla spp., Bemisia spp., Trialeurodes spp., gphig spp., gzggg spp., Megoura viciae, Phylloxera spp., Adelges spp., Phorodon humuli (hop damson aphid), Aeneolamia spp., ephotettix spp. (rice leaf hoppers), Empoasca spp., Nilaparvata spp., Perkinsiella spp., Pxrilla spp., Aonidiella spp. (red scales), Coccus spp., gggggggggg spp., Helopeltis spp. (mosquito bugs), gxggg spp., Dzsdercus spp., Ogycarenus-spp., Nezara spp.; Hymenoptera e.g. Athalia spp. and Cephus spp. (saw flies), gggg spp. (leaf cutting ants); Diptera e.g. Hylemzia spp. (root flies), Atherigona spp. and Chlorops spp. (shoot flies), Phytomyza spp. (leaf miners), Ceratitis spp. (fruit flies); Thysanoptera such as Thrips tabaci; Orthoptera such as Locusta and Schistocerca spp. (locusts) and crickets e.g. Gryllus Erimitivus); dagger nematodes such as Xiphinema spp. (e.g. g. diyersicaudatum), Longidorus spp. (e.g. ;. elongatus); Hoplglaimus spp. (e.g. g. coronatus); Aphelenchoides spp. (e.g. 5. ritzema-bosi, 5. besseyi); stem and bulb eelworms such as Ditylenchus spp. (e.g.
Q. dipsaci).
The invention also provides a method for the control of arthropod or nematode pests of plants which comprises the application to the plants or to the medium in which they grow of an effective amount of the compound of formula (I).
For the control of arthropods and nematodes, the active compound is generally applied to the locus in which arthropod or nematode infestation is to be controlled at a rate of 0.1kg to 25kg of active compound per hectare of locus treated. Under ideal conditions, depending on the pest to be controlled, the lower rate may offer adequate protection. On the other hand, adverse weather conditions, resistance of the pest and other factors may require that the active ingredient be used in higher proportions. In foliar application, a rate of lg to l0O0g/ha may be used.
When the pest is soil-borne, the formulation containing the active compound is distributed evenly over the area to be treated in any convenient manner.
Application may be made, if desired, to the field or -10.. crop-growing area generally or in close proximity to the seed or plant to be protected from attack. The active component can be washed into the soil by spraying with water over the area or can be left to the natural action of rainfall. During or after application, the formulation can, if desired, be distributed mechanically in the soil, for example by ploughing or disking. Application can be prior to planting, at planting, after planting but before sprouting has taken place or after sprouting.
The compound of _ formula (I) may be applied in solid or liquid compositions to the soil ‘principally to control those nematodes dwelling therein but also to the foliage principally to control those nematodes attacking the aerial parts of the plants (e.g. Aphelenchoides spp. and Ditylenchus spp. listed above). V .
The compound of formula (I) is of value in controlling pests which feed on parts of the plant remote from the point of application, e.g. leaf feeding insects are killed by the subject compounds applied to roots.
In addition the compound may reduce attacks on the plant by means of antifeeding or repellent effects.
The compound of formula (I) is of particular value in the protection of field, forage, plantation, glasshouse, orchard and vineyard crops, of ornamentals and of plantation and forest trees, for example, cereals (such as maize, wheat, rice, sorghum), cotton, tobacco, vegetables and salads (such as beans, cole crops, curcurbits, lettuce, onions, tomatoes and peppers), field crops (such as potato, sugar beet, ground nuts, soyabean, oil seed rape), sugar cane, grassland and forage (such as maize, sorghum, lucerne), plantations (such as of tea, coffee, cocoa, banana, oil palm, coconut, rubber, spices), orchards and groves (such as of stone and pip fruit, citrus, kiwifruit, avocado, mango, olives and walnuts), vineyards, ornamental plants, flowers and shrubs under glass and in gardens and parks, forest trees (both deciduous and evergreen) in forests, plantations and nurseries.
It is also valuable in the protection of timber (standing, felled, converted, stored or structural) from attack by sawflies (e.g. Urocerus) or beetles (e.g. scolytids, platypodids, lyctids, bostrychids, cerambycids, anobiids), or termites, for example, Reticulitermes spp., Heterotermes spp., Coptotermes spp.
It has applications in the protection of stored products such as grains, fruits, nuts, spices and tobacco, whether whole, milled or compounded into products, from moth, beetle and mite attack. Also _ 12 - protected are stored animal products such as skins, hair, wool and feathers in natural or converted form (e.g. as carpets or textiles) from moth and beetle attack; also stored meat and fish from beetle, mite and fly attack.
The compound of formula (I) is of ‘particular value in the control of arthropods, helminths or protozoa which are'injurious to, or spread or act as vectors of diseases in man and domestic animals, for example those hereinbefore mentioned, and more especially in the control of ticks, mites, lice, fleas, midges and biting, nuisance and myiasis flies.
The compound of formula (I) is particularly useful in controlling arthropods, helminths or protozoa which are present inside domestic host animals or which feed in or on the skin or suck the blood of the animal, for which purpose they may be administered orally, parenterally, percutaneously or topically.
Coccidiosis, a disease caused by infections by protozoan parasites of the genus Eimeria, is an important potential cause of economic-loss in domestic animals and birds, particularly those raised or kept under intensive conditions. For example, cattle, sheep, pigs and rabbits may be affected, but the disease is especially important in poultry, in particular chickens.
The poultry disease is generally spread by the birds picking up the infectious organism in droppings on contaminated litter or ground or by way of food or drinking water. The disease is manifested by hemorrhage, accumulation of blood in the ceca, passage of blood to the droppings, weakness and digestive disturbances. The disease often terminates in the death of the animal but the fowl'which survive severe infections have had their market value substantially reduced as a result of the infection.
Administration of a small-amount of the compound of formula (1) preferably by combination with poultry feed is effective in preventing or greatly reducing the incidence of coccidiosis. The compound The compound of formula (I) also exerts an inhibitory effect on the oocysts by greatly reducing the number and or the sporulation of those produced.
The compositions hereinafter described for topical application to man and animals and in the protection of stored products, household goods, property and areas of the general environment may, in general, alternatively be employed for application to growing crops and crop growing loci and as a seed dressing.
Suitable means of applying the compound of formula (I) include: — to persons or animals infested by or exposed to infestation by arthropods, helminths or protozoa, by parenteral, oral or topical application of compositions in which the active ingredient exhibits an immediate and/or prolonged action over a period of time against the arthropods, helminths or protozoa, for example by incorporation in feed or suitable orally-ingestible pharmaceutical formulations, edible baits, salt licks, dietary supplements, pour—on formulations, sprays, baths, dips, showers, jets, dusts, greases, shampoos, creams, wax-smears and livestock self-treatment systems; to the environment in general or to specific locations where pests may lurk, including stored products, timber, household goods, and domestic and industrial premises, as sprays, fogs, dusts, smokes, wax-smears, lacquers, granules and baits, and in tricklefeeds to waterways, wells, reservoirs and other running or standing water; to domestic animals in feed to control fly larvae feeding in their faeces; to growing crops as foliar sprays, dusts, granules, fogs and foams; also as suspensions of finely divided and encapsulated compound of formula (I); as soil and root treatments by liquid drenches, dusts, granules, smokes and foams; and as seed dressings by liquid slurries and dusts.
The compound of formula (l) may be applied to control arthropods, helminths or protozoa in compositions of any type known to the art suitable for internal or external administration to vertebrates or application for the control of arthropods in any premises or indoor or outdoor area, containing as active ingredient the compound of formula (I) in association with one or more compatible diluents or adjuvants appropriate for the intended use.
All such compositions may be prepared in any manner known to the art.
Compositions suitable for administration to vertebrates or man include preparations suitable for oral, parenteral, percutaneous, e.g. pour—on, or topical administration.
Compositions for oral administration comprise the compound of formula (I) in association with pharmaceutically acceptable carriers or coatings and include, for example, tablets, pills, capsules, pastes, gels, drenches, medicated feeds, medicated drinking water, medicated dietary supplements, slow-release boluses or other slow-release devices intended to be retained within the gastro-intestinal tract. Any or these may incorporate active ingredient contained within microcapsules or coated with acid-labile or alkali—labile or other pharmaceutically acceptable enteric coatings. Feed premixes and concentrates containing compounds of the present invention for use in preparation of medicated diets, drinking water or other materials for consumption by animals may also be used.
Compositions for parenteral administration include solutions, emulsions or suspensions in any suitable pharmaceutically acceptable vehicle and solid or semisolid subcutaneous implants or pellets designed to release active ingredient over a protracted period and may be prepared and made sterile in any appropriate ‘manner known to the art.
’ Compositions for percutaneous and topical administration include sprays, dusts, baths, dips, showers, jets, greases, shampoos, creams, wax-smears, or pour-on preparations and devices (e.g. ear tags) attached externally to animals in such a way as to provide local or systemic arthropod control. _ 17 _ Solid or liquid baits suitable for controlling arthropods comprise the compound of formula (I) and a carrier or diluent which may include a food substance or some other substance to induce comsumption by the arthropod.
Liquid compositions include water miscible concentrates, emulsifiable concentrates, flowable suspensions, wettable or soluble'powders containing the compound of formula (I) which may be used to treat substrates or sites infested or liable to infestation by arthropods including premises, outdoor or indoor storage or processing areas, containers or equipment and standing or running-water.
Solid homogenous or heterogenous compositions containing the compound of formula (I), for example granules, pellets, briquettes or capsules, may be used to treat standing or running water over a period of time. A similar effect may be achieved using trickle or intermittent feeds of water dispersible concentrates as described herein.
Compositions in the form of aerosols and aqueous or non-aqueous solutions or dispersions suitable for spraying, fogging and low- or ultra-low volume spraying may also be used.
Suitable solid diluents which may be used in the preparation of compositions suitable for applying the _ 18 _ compound of formula (I) include aluminium silicate, kieselguhr, corn husks, tricalcium phosphate, powdered cork, absorbent carbon black, magnesium silicate, a clay such as kaolin, bentonite or attapulgite, and water soluble polymers and such solid compositions may, if desired, contain one or more compatible wetting, dispersing,.emu1sifying or colouring agents which, when solid, may also serve as diluent.
Such solid compositions, which may take the form of dusts, granules or wettable powders, are generally prepared by impregnating the solid diluents with solutions of the compound of formula (I) in volatile solvents, evaporating the solvents and, if necessary, grinding the products so as to obtain powders and, if desired, granulating or compacting the products so as to obtain granules, pellets or briquettes or by encapsulating finely divided active ingredient in natural or synthetic polymers, e.g. gelatin, synthetic resins and polyamides.
The wetting, dispersing and emulsifying agents which may be present, particularly in wettable powders, may be of the ionic or non-ionic types, for example sulphoricinoleates, quaternary ammonium derivatives or products based upon condensates of ethylene oxide with nonyl- and octyl-phenol, or carboxylic acid esters of _ 19 _ anhydrosorbitols which have been rendered soluble by etherification of the free hydroxy groups by condensation with ethylene oxide, or mixtures of these types of agents. Wettable powders may be treated with water immediately before use to give suspensions ready for application.
Liquid compositions for the application of the compound of formula (I)‘may take the form of solutions, suspensions and emulsions of the compound of formula (I) optionally encapsulated in natural or synthetic polymers, and may, if desired, incorporate wetting, dispersing or emulsifying agents.
These emulsions, suspensions and solutions may be prepared using aqueous, organic or aqueous-organic diluents, for example acetophenone, isophorone, toluene, xylene, mineral, animal or vegetable oils, and water soluble polymers (and mixtures of these diluents), which may contain wetting, dispersing or emulsifying agents of the ionic or non-ionic types or mixtures thereof, for example those of the types de- scribed above. When desired, the emulsions containing the compound of formula (I) may be used in the form of self-emulsifying concentrates containing the active substance dissolved in the emulsifying agents or in solvents containing emulsifying agents compatible with the active substance, the simple addition of water _ 20 _ to such concentrates producing compositions ready for use.
Compositions containing the compound of formula (I) which may be applied to control arthropod, plant nematode, helminth or protozoan pests, may also contain synergists (e.g. piperonyl butoxide or sesamex), stabilizing substances, other insecticides, acaricides, plant nematocides,-anthelmintics or anticoccidials, fungicides (agricultural or veterinary as apropriate e.g. benomyl, iprodione), bactericides, arthropod or vertebrate attractants or repellents or pheromones, reodorants, flavouring agents, dyes and auxiliary therapeutic agents, e.g. trace elements.
These may be designed to improve potency, persistence, safety, uptake where desired, spectrum of pests controlled or to enable the composition to perform other useful functions in the same animal or area treated. V Examples of other pesticidally-active compounds which may be included in, or used in conjunction with, the compositions of the present invention are:- acephate, chlorpyrifos, demeton-S-methyl, disulfoton, ethoprofos, fenitrothion, malathion, monocrotophos, parathion, phosalone, pirimiphos-methyl, triazophos, cyfluthrin, cypermethrin, deltamethrin, fenpropathrin, fenvalerate, permethrin, aldicarb, carbosulfan, _ 21 _ methomyl, oxamyl, pirimicarb, bendiocarb, teflubenzuron, dicofol, endosulfan, lindane, benzoximate, cartap, cyhexatin, tetradifon, avermectins, ivermectin, milbemycins, thiophanate, trichlorfon, dichlorvos, diaveridine and dimetridazole.
The compositions for application to control arthropod, plant nematode, helminth or protozoan pests usually contain from 0.0000l% to 95%, more particularly from 0.0005% to to 50%, by weight of the compound of formula (I) together with other substances toxic to arthropods and plant nematodes, anthelmintics, anticoccidials, synergists, trace elements or stabilisers. The actual compositions employed and their rate of application will be selected to achieve the desired effect(s) by the farmer, livestock producer, medical or veterinary practitioner, pest control operator or other person skilled in the art. Solid and liquid compositions for application topically to animals, timber, stored products or household goods usually contain from 0.00005% to 90%, more particularly from 0.001% to 10%, by weight of the compound of formula (I). For administration to animals orally or parenterally, including percutaneously solid and liquid compositions normally contain from 0.1% to 90% by - 22 _ weight of the compound of formula (I). Medicated feedstuffs normally contain from 0.001% to 3% by weight of the compound of formula (I).
Concentrates and supplements for mixing with feedstuffs normally contain 5% to 90%, and preferably from 5% to 50%, by weight of the compound of formula (I). Mineral salt licks normally contain from 0.1% to lO% by weight of the compound of formula (I).
Dusts and liquid compositions for application to livestock, persons, goods, premises-or outdoor areas may contain 0.000l% to 15%, and more especially 0.005% to 2. %, by weight of the compound of formula (I). Suitable concentrations in treated waters are between 0.0001 ppm and 20 ppm, and more especially 0.001 ppm to 5.0 ppm. of the compound of formula (I) and may also be used therapeutically in fish farming with appropriate exposure times. Edible baits may contain from 0.01% to % and preferably 0.01% to 1.0%, by weight of the compound of formula (I). when administered to vertebrates parenterally, orally or by percutaneous or other means, the dosage of the compound of formula (I) will depend upon the species, age and health of the vertebrate and upon the nature and degree of its actual or potential infestation by arthropod, helminth or protozoan pest.
A single dose of 0.1 to 100 mg, preferably 2.0 to 20.0 mg, per kg body weight of the animal or doses of 0.01 to 20.0 mg, preferably 0.1 to 5.0 mg, per kg body weight of the animal per day for sustained medication are generally suitable by oral or parenteral administration. By use of sustained release formulations or devices, the daily doses required over a period of months may be combined and administered to animals on a single occasion.
In experiments on activity against arthropods carried out on the compound of formula (I), the following results (wherein ppm indicates the concentration of the compound in parts per million of the test solution applied) have been obtained: — E One or more dilutions of the compound of formula (I) were made in 50% aqueous acetone. (a) Test species: Plutella xylostella (Diamond back Moth).
Turnip leaf discs were set in agar in petri—dishes and infected with 10 larvae (2nd instar Plutella). Four replicate dishes were assigned to each treatment and were sprayed Four or with the appropriate test dilutions. five days after treatment the dishes were removed from the constant temperature (25°C) room in which they had been held and the mean percentage rnortalities of larvae were determined. These data were corrected against the moxtalities in dishes treated with 50% aqueous acetone alone which served as controls.
According to the above method an application of the compound of fonnula (I) was effective against the larvae‘ ofP1utel1a xylostella producing at least 65% mortality at less than 500 ppm. _ 25 _ The following Composition Examples illustrate "compositions for use against arthropod, plant nematode, helminth or protozoan pests which comprise, as active ingredient, the compound of formula (I). The compositions described in Composition Examples 1 to 6 can each he diluted in water to give a sprayable composition at concentrations suitable for use in the field.
COMPOSITION EXAMPLE 1 A water soluble concentrate was prepared from the compound of formula (I) 7% w/v Ethylan BCP 10% w/v and E-methylpyrrolidone to 100% by volume by dissolving the Ethylan BCP in a portion of g-methylpyrrolidone, and then adding the active ingredient with heating and stirring until dissolved.
The resulting solution was made up to volume by adding the remainder of the solvent.
COMPOSITION EXAEPLE 2 An emulsifiable concentrate was prepared from the compound of formula (I) 7% W/V Soprophor BSU 4% w/v Arylan CA 4% w/v g-methylpyrrolidone 50% w/v and Solvesso 150 to 100% by volume by dissolving Soprophor BSU, Arylan CA and the active ingredient in E-methylpyrrolidone, and then adding solvesso 150 to volume.
COMPOSITION EXAMPLE 3 A wettable powder was prepared from the compound of formula (I) 40% w/w Arylan S 2% w/w Darvan No. 2 5% w/w and Celite PF to 100% by weight by mixing the ingredients, and grinding the mixture in a hammer-mill to a particle size less than 50 microns.
COMPOSITION EXAMPLE 4 An aqueous flowable formulation was prepared from the compound of formula (I) 30% w/v Ethylan BCP ‘ 1% w/v Sopropon T36 0.2% w/v Ethylene glycol 5% w/v Rhodigel 23 0.15% w/v and water to 100% by volume by intimately mixing the ingredients and grinding in a bead mill until the median particle size was less than microns. _ 27 _ COMPOSITION EXAMPLE 5 An emulsifiable suspension concentrate was prepared from the compound of formula (I) 30% w/V Ethylan BCP l0% w/v Bentone 38 0.5% W/V and Solvesso 150 to 100% by volume by intimately mixing the ingredients and grinding in a bead mill until the median particle size was less than 3 microns.
COMPOSITION EXAMPLE 6 Water dispersible granules were prepared from the compound of formula (I) 30% w/w Darvan No. 2 15% w/w Arylan S 8% w/w and Celite PF to 100% by weight by mixing the ingredients, micronising in a fluid-energy mill, and then granulating in a rotating pelletiser by spraying on sufficient water (up to 10% w/w). The resulting granules were dried in a fluid—bed drier to remove excess water. _ 23 - Descriptions of commercial ingredients used in the foregoing Composition Examples:- Ethylan BCP nonylphenol ethylene oxide condensate Soprophor BSU condensate of tristyrylphenol and ethylene oxide Arylan CA 70% w/v solution of calcium dodecylbenzenesulphonate Solvesso 150 light Clo-aromatic solvent Arylan S sodium dodecylbenzenesulphonate Darvan sodium lignosulphonate Celite PF synthetic magnesium silicate carrier Sopropon T36 sodium salt of polycarboxylic acid Rhodigel 23 polysaccharide ianthan gum Bentone 38 organic derivative of magnesium montmorillonite COMPOSlTION EXAMPLE 7 A dusting powder may be prepared by intimately mixing:- the compound of formula (I) l l to 10% w/w (weight/weight) Talc superfine to 100% by weight This powder may be applied to a locus of arthropod infestation, for example refuse tips or dumps, stored products or household goods or animals- infested by, or at risk of infestation by, arthropods to control the arthropods by oral ingestion. Suitable _ 29 _ means for distributing the dusting powder to the locus of arthropod infestation include mechanical blowers, handshakers and livestock self treatment devices.
COMPOSITION EXAMPLE 8 An edible bait may be prepared by intimately mixing:- the compound of formula (l) 0-1 to 1.0% W/W wheat flour 80% w/w Molasses to 100% w/w This edible bait may be distributed at a locus, for example domestic and industrial premises, e.g. kitchens, hospitals or stores, or outdoor areas, infested by arthropods, for example ants, locusts, cockroaches and flies, to control the arthropods by oral ingestion.
A solution may be prepared containing:- the compound of formula (I) % w/V (weight/volume) Dimethylsulphoxide to 100% by volume by dissolving the pyrazole derivative in a portion of the dimethyl-sulphoxide and then adding more dimethylsulphoxide to the desired volume. This solution may be applied to domestic animals infested by - 30 _ arthropods, percutaneously as a pour-on application or, after sterilisation by filtration through a polytetrafluoroethylene membrane (0.22 micrometre pore size), by parenteral injection, at a rate of application of from 1.2 to 12 ml of solution per 100 kg of animal body weight.
COMPOSITION EXAMPLE 10 A wettable powder may be formed from:- the compound of formula (I) 50% w/w Ethylan BCP (a nonylphenol/ethylene oxide condensate containing 9 moles of ethylene oxide per mol of phenol) 5% w/w A Aerosil (silicon dioxide of microfine-particle size) 5% w/w Celite PF (synthetic magnesium silicate carrier) ‘4o% w/w by adsorbing the Ethylan BCP onto the Aerosil, mixing with the other ingredients and grinding the mixture in a hammer-mill to give a wettable powder, which may be diluted with water to a concentration of from 0.001% to 2% w/v of the pyrazole compound and applied to a locus of infestation by arthropods, for example dipterous larvae, or plant nematodes by spraying, or to domestic animals infested by, or at risk of infestation by, arthropods, helminths or protozoa, by spraying or _ 31 _ dipping, or by oral administration in drinking water, to control the arthropods, helminths or protozoa.
COMPOSITION EXAMPLE 11 A slow release bolus may be formed from granules containing a density agent, binder, slow- release agent and the compound of formula (I) at varying percentage compositions. By compressing the mixture a bolus-with a specific gravity of 2 or more can be formed and may be administered orally to ruminant domestic animals for retention within the reticulo-rumen to give a continual slow release of pyrazole compound over an extended period of time to control infestation of the ruminant domestic animals by arthropods, helminths or protozoa.
COMPOSITION EXAMPLE 12 A slow release composition may be prepared from:- the compound of formula (I) 0.5 to 25% W/W polyvinylchloride base to 100% w/w by blending the polyvinylchloride base with the pyrazole compound and a suitable plasticiser, e.g. dioctyl phthalate, and melt-extruding or hot-moulding the homogenous composition into suitable shapes, e.g. granules, pellets, brickettes or strips, suitable, for example, for addition to standing water or, in the case of strips, fabrication into collars or ear-tags for attachment to domestic animals, to control insect pests by slow release of the pyrazole compound.
The compound of formula (I) can be prepared by the application or adaptation of known methods (ie. methods heretofore used or described in the chemical literature), generally pyrazole ring formation followed where necessary by changing substituents. A description of its preparation is given in Example 1 which follows.
The following Example and Reference Examples illustrate the preparation of the compound of formula (I) according to the present invention: [Chromatography was effected on a silica column (May & Baker Ltd 40/60 flash silica) at a pressure of 6.8Nm'2, unless otherwise stated] EXAMPLE 1 A partial solution of 5-aminocyano-l-(2,6-dichlorotrifluoromethy|phenyl) trifluoromethylthiopyrazole (48.0g) in chloroform (600ml) was stirred mechanically and treated with m-chloroperbenzoic acid (61 .4g). The mixture was stirred and heated under reflux in an atmosphere of nitrogen for 3.5 hours. After cooling, an additional amount of m-chloroperbenzoic acid (l2.3g) was added, and reflux continued for 1 hour. The cooled mixture was diluted with ethyl acetate (600ml), washed with a solution of sodium metabisulphite (2 x 250ml), then with sodium hydroxide solution (2 x 250ml) and finally with water ‘I x 500ml). The organic layer was dried over anhydrous magnesium sulphate, filtered, and evaporated in vacuo to give a fawn solid.
Recrystallisation from toluene/hexane/ ethyl acetate gave 5-amino—3—cyano-1—(2,6- dichlorotrifluoromethylphenyl)trifluoromethanesulphonylpyrazole as white crystals (37.0g) m.p. 219-22l.S°C.
REFERENCE EXAMPLE 1 A solution of 5-aminocyano-l-(2,6-dichlorotrifluoromethylphenyl)pyrazole (20.0g) in dichloromethane (l00ml) was stirred magnetically and treated dropwise with a solution of trifluoromethylsulphenyl chloride (l0.8g) in dichloromethane (501111) during 1 hour. The solution was stirred overnight at room temperature , then washed with water (lO0m1), dried over anhydrous magnesium sulphate, filtered, and evaporated in vacuo to give a solid (26.3g). This solid was recrystallised from .34- toluene/hexane to give S-aminocyano(2,6-dichloro—4-trifluoromethylphenyl)-LL trifluoromethylthiopyrazole as fawn crystals (24.2g) m.p. 169-171 °C.
REFERENCE EXAMPLE 2 -Aminocyano(2,6-dichloro—4-trifluoromethylphenybpyrazole used in the above Reference Example was prepared as follows: A suspension of nitrosyl sulphuric acid prepared from sodium nitrite (7.0g) and concentrated sulphuric acid (27.5ml) was diluted with acetic acid (25ml), cooled to °C, and stirred mechanically. To this was added a solution of 2,6-dichloro-4» trifluoromethylaniline (212g) in acetic acid (50ml) dropwise over 15 minutes at 25- 32°C. This mixture was heated to 55 °C for 20 minutes and poured onto a stirred solution of ethyl 2,3-dicyanopropionate (14.0g) in acetic acid (60ml) and water (125ml) at 10-20°C. After 15 minutes, water (200ml) was added, and the oily layer separated. The aqueous solution was then extracted with dichloromethane (3 x 70ml) and the extracts combined with the oil and washed with ammonia solution (to pH9).
The organic phase was then stirred with ammonia (20ml) for 2 hours, and the dichloromethane layer then separated. This was washed with water (1 x 100ml), 1N hydrochloric acid (1 x 100ml), dried over anhydrous magnesium sulphate, filtered, and evaporated in vacuo to give an oily solid. Crystallisation from to-luene/hexane gave the title compound as brown crystals (20.9g), m.p. 140-142°C.
REFERENCE EXAMPLE 3 To a stirred solution of S-aminocyano-l-(2,6-dichloro trifluoromethylphenyl)pyrazole (2.23 g) and pyridine (0.55g) in chloroform (50ml) was added dropwise at 0°C, a solution of trifluoromethylsulphenyl chloride (1.24g) in chloroform (1Sml) during 20 minutes. The mixture was stirred at 0°C for 3 hours, and the solvent evaporated in vacuo to give a yellow solid (3.1 g). This was purified by chromatography on silica (Merck, 230-400 mesh, 0.7 kgcrn‘2) eluting with dichloromethane and petroleum ether b. 40-60° (3: 1) to give 5-amino(2,6- dichlorotn'fluoromethylphenyl)~3-cyanotrifluoromethylthiopyrazoIe in the form ofa white solid (2.33g), m.p. 169.5~170.5°C.
Claims (4)
1. An arthropodicidal, plant nematocidal, anthelmintic or anti-protozoal composition which comprises an N-phenylpyrazole derivative of the formula; R‘ CN / ‘N HQN N’ '2 R (1) wherein R‘ represents trifluoromethanesulphonyl or trifluoromethylthio and R2 represents 2,6-dichlorotrifluoromethylphenyl in association with one or more compatible diluents or carriers.
2. 5-Amino(2,6-dichlorotrifluoromethylphenyl)cyano trifluoromethylsulphonylpyrazole.
3. A method for the control of arthropod, plant nematode, helminth or protozoa] pests at a locus which comprises treatment of the locus with an effective amount of a compound as defined in claim 1, with the exclusion of a method for the treatment of the human or animal body carried out by a medical or veterinary practitioner as therapy.
4. A compound of the general formula (I) as defined in claim 1 for use in the manufacture of a medicament for the treatment of an arthropod, helminth or protozoal infection. F. R. KELLY & CO., AGENTS FOR THE APPLICANTS
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Application Number | Priority Date | Filing Date | Title |
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GBUNITEDKINGDOM12/06/19878713768 | |||
GB878713768A GB8713768D0 (en) | 1987-06-12 | 1987-06-12 | Compositions of matter |
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IE20020481A1 IE20020481A1 (en) | 2004-02-11 |
IE84607B1 true IE84607B1 (en) | 2007-06-13 |
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